tert-Butyl (2E)-3-(5-benzyloxy-6-methylpyridin-2-yl)acrylate → tert-Butyl 3-(5-hydroxy-6-methylpyridin-2-yl)propanoate

HRID 1820955Notes

Reaction equation

HRID 1820955 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12](/[CH:16]=[CH:17]/[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[N:13][C:14]=1[CH3:15])C1C=CC=CC=1>CCO.[OH-].[OH-].[Pd+2]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:16][CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[N:13][C:14]=1[CH3:15]

Participants

4

Reactant 1

HCID 86623614tert-Butyl (2E)-3-(5-benzyloxy-6-methylpyridin-2-yl)acrylate

Product 1

HCID 68851078tert-Butyl 3-(5-hydroxy-6-methylpyridin-2-yl)propanoateYield 88.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A solution of 700 mg (2.15 mmol) of tert-butyl (2E)-3-(5-benzyloxy-6-methylpyridin-2-yl)acrylate (from Step C) and 100 mg of 20% palladium hydroxide on carbon in 20 mL of EtOH was stirred under 1 atm of H2 overnight. The catalyst was filtered off through a cake of Celite and washed extensively with EtOAc. The filtrate was concentrated. Chromatography on a Biotage 40M cartridge using 7:13 v/v EtOAc/hexanes as the eluant afforded 450 mg of the title compound: 1H NMR (500 MHz, CDCl3) δ 1.41 (s, 9H), 2.49 (s, 3H), 2.63 (d, J=7.4, 2H), 2.98 (d, J=7.4, 2H), 6.90 (d, J=8.3, 1H), 7.05 (d, J=8.3, 1H).

Workup

  1. filtrationThe catalyst was filtered off through a cake of Celite
  2. washwashed extensively with EtOAc
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-4540708cc5694d2a88f23fab754202a0
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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